Glycerin-based surfactants such as glycerin alkyl ether are utilized in various fields, such as foods, cosmetics, medicaments, and the like, for their excellent functions as a nonionic surfactant.
Known producing methods of glycerin alkyl ether include, for example, a ring-opening polymerization of glycidol with alcohol in the presence of a basic catalyst, addition of alkyl glycidyl ether to polyglycerin (Patent Document 1), addition of olefin to polyglycerin (Patent Document 2), and the like.
As a purification method of the reaction product, a chromatographic separation is known. For example, a method to bring crude alkyl glucoside containing higher alcohol as an impurity into contact with silica gel or synthetic adsorbent, followed by separating the higher alcohol and alkyl glucoside by a simulated moving bed chromatography (Patent Document 3), a method to adsorb a mixture containing at least two kinds of higher aliphatic compounds selected from higher aliphatic hydrocarbon, higher fatty acid complete ester, higher aliphatic alcohol, higher fatty acid partial ester, and higher aliphatic nonionic surfactant onto a column filled with silica gel, followed by eluting the component sequentially from more hydrophobic higher aliphatic compound by passing a plurality of organic solvents with different hydrophobicity sequentially from more hydrophobic solvent (Patent Document 4), a method to remove a low molecular weight component from a polyglycerin mixture using a particular ion exchange resin and water (Patent Document 5), and the like have been proposed.